title: Design, synthesis and biological activities of some 7-aminocephalosporanic acid derivatives.
abstract: The treatment of 7-ACA with 4-substituted benzensulfonyl chlorides afforded the compounds containing 4-nitro/aminophenyl sulfonylamino moiety in the cephalosporanic acid skeleton (2, 4). The synthesis of the cephalosporanic acid derivatives containing 1,3-thiazole or 5-oxo-1,3-thiazolidine nucleus and sulfonamide function (8a, 8b, 10) was performed starting from 7-ACA by several steps. The reaction of 7-ACA with [4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]acetyl chloride afforded the corresponding 7-{[4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]acetyl}amino derivative (13). The synthesized compounds were screened for their antimicrobial and antiurease activities. Some of them were found to possess good-moderate antimicrobial activity against the test microorganisms. Compound 5d was observed to have moderate anti-urease activity.
authors.affiliation: Karadeniz Technical University, Department of Chemistry, 61080 Trabzon, Turkey.
authors.forename: Serap
authors.initials: S
authors.lastname: Basoglu
authors.forename: Ahmet
authors.initials: A
authors.lastname: Demirbas
authors.forename: Serdar
authors.initials: S
authors.lastname: Ulker
authors.forename: Sengul
authors.initials: S
authors.lastname: Alpay-Karaoglu
authors.forename: Neslihan
authors.initials: N
authors.lastname: Demirbas
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D032449:Canavalia / Q000201:enzymology; D002511:Cephalosporins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013329:Structure-Activity Relationship; D014510:Urease / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D002511:Cephalosporins; D004791:Enzyme Inhibitors; C030735:7-aminocephalosporanic acid; D014510:Urease
keywords: 1,3-Oxazole; 1,3-Thiazole; 7-Aminocephalosporanic acid; Anti β-lactamase activity; Anti-urease activity; Antimicrobial activity